(3S,3aS,5S,6E,9R,10E,11aS)-5,9-dihydroxy-3,6,10-trimethyl-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-2-one

Details

• Internal ID: d3121c76-4f57-43cd-b2c4-23840ee10471
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (3S,3aS,5S,6E,9R,10E,11aS)-5,9-dihydroxy-3,6,10-trimethyl-3a,4,5,8,9,11a-hexahydro-3H-cyclodeca[b]furan-2-one
• InChI: InChI=1S/C15H22O4/c1-8-4-5-12(16)9(2)6-14-11(7-13(8)17)10(3)15(18)19-14/h4,6,10-14,16-17H,5,7H2,1-3H3/b8-4+,9-6+/t10-,11-,12+,13-,14+/m0/s1
• InChI Key: BDIVIJRCFBPADM-FKVVBQFKSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.57
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9895	98.95%
Caco-2	+	0.7211	72.11%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5894	58.94%
OATP2B1 inhibitior	-	0.8549	85.49%
OATP1B1 inhibitior	+	0.9305	93.05%
OATP1B3 inhibitior	+	0.9561	95.61%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9082	90.82%
P-glycoprotein inhibitior	-	0.9327	93.27%
P-glycoprotein substrate	-	0.8274	82.74%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8313	83.13%
CYP3A4 inhibition	-	0.8909	89.09%
CYP2C9 inhibition	-	0.9310	93.10%
CYP2C19 inhibition	-	0.8863	88.63%
CYP2D6 inhibition	-	0.9239	92.39%
CYP1A2 inhibition	-	0.7266	72.66%
CYP2C8 inhibition	-	0.9609	96.09%
CYP inhibitory promiscuity	-	0.8809	88.09%
UGT catelyzed	+	0.6362	63.62%
Carcinogenicity (binary)	-	0.9342	93.42%
Carcinogenicity (trinary)	Non-required	0.5272	52.72%
Eye corrosion	-	0.9658	96.58%
Eye irritation	-	0.8801	88.01%
Skin irritation	-	0.5426	54.26%
Skin corrosion	-	0.9215	92.15%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7289	72.89%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	+	0.7625	76.25%
skin sensitisation	-	0.7321	73.21%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.6313	63.13%
Acute Oral Toxicity (c)	III	0.4734	47.34%
Estrogen receptor binding	-	0.4779	47.79%
Androgen receptor binding	-	0.7272	72.72%
Thyroid receptor binding	-	0.5182	51.82%
Glucocorticoid receptor binding	+	0.7622	76.22%
Aromatase binding	-	0.7573	75.73%
PPAR gamma	-	0.6576	65.76%
Honey bee toxicity	-	0.8588	85.88%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.8923	89.23%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.07%	95.56%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	84.79%	86.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.20%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.12%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.13%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.96%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.31%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.16%	96.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.96%	96.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.61%	86.33%

Plants that contains it

• Parasenecio petasitoides

Cross-Links

• PubChem: 162899641
• LOTUS: LTS0231251
• wikiData: Q104924273